Annapolis Vacation Packages
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Your Annapolis Vacation
Pick a Annapolis vacation package and focus on what counts — having some fun. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and coastal scenery. Fill your days with tours of K Bridge Recreation Area, Crane Lake Recreation Area and Walnut Hollow Lake, some of the attractions you should see during your trip to Annapolis. A couple of quick clicks is all it takes to build a customized Annapolis vacation on Expedia.
Top Annapolis Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hermann Grain Bins BNB
CA $2,554
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
6/10 (2 reviews)
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.
Reviewed on May 22, 2026
Super 8 by Wyndham Cuba
CA $1,247
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
I was very impressed with this Super 8. It was impeccably clean. The room was spacious and relaxing. Yes, some of the furniture was showing their age but otherwise, everything was great! This might lead me to try other Super 8’s.
Reviewed on Sep 25, 2026
Ready to book your vacation to Annapolis?
Annapolis Hotel Deals
Panther Den Cabin is located 4 miles from Hwy K Campground
Annapolis. MO
9.4/10 Exceptional! (16 reviews)
"Had everything we needed just in town and we prefer a more country setting!!! Very clean!!"
Reviewed on Aug 17, 2026
Hunters/Floaters Welcome! Creekside Missouri Cabin
Annapolis MO
10/10 Exceptional! (2 reviews)
"Great weekend in a very peaceful atmosphere! Very clean! Creek was fun for 7 year-old grandson. Had fire pit and space to play games! Perfect for our needs!"
Reviewed on Jul 20, 2026
Relaxing 3B Log Home-15 min walk to the Black River!
Annapolis MO
8.8/10 Excellent! (12 reviews)
"This luxury cabin was the perfect getaway. For a remote location it has everything to keep a family busy happy and comfortable. The little details so well thought of from all the kitchen amenities to full closet of family games for the little and the older. Plenty of towels and blankets all clean ..."
Reviewed on Jun 23, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Annapolis attractions
K Bridge Recreation Area
9.6/10 (4 reviews)
Explore the great outdoors at K Bridge Recreation Area, a lovely green space in Annapolis. While you're in the area, stroll along the riverfront.
Walnut Hollow Lake
Commune with nature and explore the great outdoors at Walnut Hollow Lake during your travels in Annapolis. Wander the parks and riverfront while you're in the area.
Frequently asked questions
How much does an Annapolis vacation package cost?
Offering excellent value package deals from CA $1,142 on Expedia, you'll be pleasantly surprised at how much a vacation to Annapolis costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Annapolis?
Plan your getaway for the off-peak season and you're likely to find cheap Annapolis vacation packages. Remember that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Annapolis?
With a well-organized schedule, you can easily visit the top Annapolis sights in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Annapolis vacation for longer.
How to find the best Annapolis package deals?
Use Expedia's filter tool to find some terrific Annapolis package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Annapolis package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book an Annapolis vacation as a package?
You can enjoy significant savings on your Annapolis retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Annapolis?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Annapolis break.
How to plan a trip to Annapolis?
- Pick your dates: The things you plan to do in Annapolis and your preferred season will help you decide when to go.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Annapolis.
- Work out your trip length: Think about how long you'd like to spend discovering Annapolis. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Annapolis vacation package for you.
